# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gil104
_database_code_depnum_ccdc_archive 'CCDC 1883098'
loop_
_audit_author_name
_audit_author_address
'H. Mueller-Bunz'
;University College Dublin
Republic of Ireland
;
_audit_update_record             
;
2018-12-04 deposited with the CCDC.	2019-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 Br Cl N O2'
_chemical_formula_sum            'C19 H21 Br Cl N O2'
_chemical_formula_weight         410.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5181(2)
_cell_length_b                   11.3448(2)
_cell_length_c                   18.2344(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.143(2)
_cell_angle_gamma                90
_cell_volume                     1900.60(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10744
_cell_measurement_theta_min      4.6170
_cell_measurement_theta_max      76.7780

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    4.323
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_reflns_number            20680
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.896
_diffrn_reflns_theta_max         77.106
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7823
_reflns_number_gt                7668
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;Refined as a 2-component twin. BASF: 0.615(1) Matrix: -1 0 0  0 -1 0  1 0 1
 The crystal was first solved by the charge flipping method as implemented in 
 SHELXT. All non-hydogen atoms were located.,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0685P)²+0.2945P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3506 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.012(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7823
_refine_ls_number_parameters     436
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0123(7) 0.0886(5) 0.1585(4) 0.0254(11) Uani 1 1 d . . . . .
C2 C 0.1395(7) 0.0649(5) 0.1385(4) 0.0294(12) Uani 1 1 d . . . . .
H2 H 0.2268 0.1046 0.1635 0.035 Uiso 1 1 calc R U . . .
C3 C 0.1406(7) -0.0174(5) 0.0813(4) 0.0312(12) Uani 1 1 d . . . . .
H3 H 0.2274 -0.0323 0.0664 0.037 Uiso 1 1 calc R U . . .
C4 C 0.0141(9) -0.0762(5) 0.0471(3) 0.0370(15) Uani 1 1 d . . . . .
Br1 Br 0.01592(10) -0.19273(5) -0.02820(4) 0.0487(2) Uani 1 1 d . . . . .
C5 C -0.1151(8) -0.0548(6) 0.0666(4) 0.0379(14) Uani 1 1 d . . . . .
H5 H -0.2015 -0.0960 0.0420 0.046 Uiso 1 1 calc R U . . .
C6 C -0.1162(7) 0.0279(6) 0.1227(4) 0.0327(13) Uani 1 1 d . . . . .
H6 H -0.2036 0.0434 0.1369 0.039 Uiso 1 1 calc R U . . .
N1 N 0.0006(5) 0.1714(5) 0.2144(3) 0.0271(9) Uani 1 1 d . . . . .
H1N1 H -0.0774 0.1673 0.2317 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1000(6) 0.2574(5) 0.2441(3) 0.0232(10) Uani 1 1 d . . . . .
O1 O 0.2130(4) 0.2749(4) 0.2276(3) 0.0298(9) Uani 1 1 d . . . . .
O2 O 0.0481(4) 0.3217(4) 0.2936(2) 0.0260(8) Uani 1 1 d . . . . .
C8 C 0.1373(6) 0.4187(5) 0.3326(4) 0.0275(11) Uani 1 1 d . . . . .
C9 C 0.1564(6) 0.5138(5) 0.2775(3) 0.0269(11) Uani 1 1 d . . . . .
C10 C 0.0620(6) 0.5243(6) 0.2049(4) 0.0292(12) Uani 1 1 d . . . . .
H10 H -0.0139 0.4684 0.1884 0.035 Uiso 1 1 calc R U . . .
C11 C 0.0774(7) 0.6153(6) 0.1564(5) 0.0395(14) Uani 1 1 d . . . . .
H11 H 0.0141 0.6206 0.1067 0.047 Uiso 1 1 calc R U . . .
C12 C 0.1863(9) 0.6978(6) 0.1816(6) 0.0499(19) Uani 1 1 d . . . . .
H12 H 0.1974 0.7604 0.1490 0.060 Uiso 1 1 calc R U . . .
C13 C 0.2791(8) 0.6902(6) 0.2536(5) 0.0479(17) Uani 1 1 d . . . . .
H13 H 0.3525 0.7481 0.2706 0.057 Uiso 1 1 calc R U . . .
C14 C 0.2648(8) 0.5971(6) 0.3017(5) 0.0409(15) Uani 1 1 d . . . . .
H14 H 0.3296 0.5911 0.3510 0.049 Uiso 1 1 calc R U . . .
C15 C 0.0477(7) 0.4670(6) 0.3846(4) 0.0362(13) Uani 1 1 d . . . . .
H15A H 0.0454 0.4063 0.4233 0.043 Uiso 1 1 calc R U . . .
H15B H 0.0991 0.5365 0.4117 0.043 Uiso 1 1 calc R U . . .
C16 C -0.1085(7) 0.5029(6) 0.3464(4) 0.0343(12) Uani 1 1 d . . . . .
H16A H -0.1109 0.5496 0.3002 0.041 Uiso 1 1 calc R U . . .
H16B H -0.1687 0.4315 0.3308 0.041 Uiso 1 1 calc R U . . .
C17 C -0.1713(7) 0.5758(6) 0.4003(4) 0.0341(12) Uani 1 1 d . . . . .
H17A H -0.1177 0.6513 0.4111 0.041 Uiso 1 1 calc R U . . .
H17B H -0.1576 0.5328 0.4490 0.041 Uiso 1 1 calc R U . . .
C18 C -0.3327(8) 0.6009(6) 0.3671(4) 0.0392(14) Uani 1 1 d . . . . .
H18A H -0.3867 0.5260 0.3536 0.047 Uiso 1 1 calc R U . . .
H18B H -0.3470 0.6492 0.3205 0.047 Uiso 1 1 calc R U . . .
Cl1 Cl -0.39985(16) 0.67930(16) 0.43749(9) 0.0406(3) Uani 1 1 d . . . . .
C19 C 0.2810(8) 0.3696(6) 0.3829(4) 0.0379(14) Uani 1 1 d . . . . .
H19A H 0.2600 0.3079 0.4161 0.057 Uiso 1 1 calc R U . . .
H19B H 0.3358 0.4333 0.4139 0.057 Uiso 1 1 calc R U . . .
H19C H 0.3389 0.3364 0.3506 0.057 Uiso 1 1 calc R U . . .
C20 C 0.4775(6) 0.8943(5) 0.8436(4) 0.0255(12) Uani 1 1 d . . . . .
C21 C 0.3478(7) 0.9062(6) 0.8647(4) 0.0310(12) Uani 1 1 d . . . . .
H21 H 0.2668 0.8574 0.8422 0.037 Uiso 1 1 calc R U . . .
C22 C 0.3372(7) 0.9900(6) 0.9187(4) 0.0333(12) Uani 1 1 d . . . . .
H22 H 0.2499 0.9976 0.9344 0.040 Uiso 1 1 calc R U . . .
C23 C 0.4542(8) 1.0615(6) 0.9493(3) 0.0343(12) Uani 1 1 d . . . . .
Br2 Br 0.43874(9) 1.17507(6) 1.02445(5) 0.04719(18) Uani 1 1 d . . . . .
C24 C 0.5822(8) 1.0535(6) 0.9285(4) 0.0370(13) Uani 1 1 d . . . . .
H24 H 0.6613 1.1045 0.9502 0.044 Uiso 1 1 calc R U . . .
C25 C 0.5938(6) 0.9688(6) 0.8747(4) 0.0313(12) Uani 1 1 d . . . . .
H25 H 0.6815 0.9621 0.8593 0.038 Uiso 1 1 calc R U . . .
N2 N 0.5005(5) 0.8087(5) 0.7914(3) 0.0291(10) Uani 1 1 d . . . . .
H1N2 H 0.5829 0.8136 0.7783 0.035 Uiso 1 1 calc R U . . .
C26 C 0.4104(6) 0.7206(5) 0.7597(4) 0.0264(11) Uani 1 1 d . . . . .
O3 O 0.2853(5) 0.7067(4) 0.7619(3) 0.0336(10) Uani 1 1 d . . . . .
O4 O 0.4824(5) 0.6500(4) 0.7214(3) 0.0343(10) Uani 1 1 d . . . . .
C27 C 0.4038(8) 0.5555(6) 0.6730(5) 0.0371(15) Uani 1 1 d . . . . .
C28 C 0.3536(7) 0.4641(5) 0.7233(4) 0.0354(13) Uani 1 1 d . . . . .
C29 C 0.2196(9) 0.4072(7) 0.6988(5) 0.0436(15) Uani 1 1 d . . . . .
H29 H 0.1541 0.4286 0.6518 0.052 Uiso 1 1 calc R U . . .
C30 C 0.1819(9) 0.3190(7) 0.7433(5) 0.0476(17) Uani 1 1 d . . . . .
H30 H 0.0904 0.2808 0.7264 0.057 Uiso 1 1 calc R U . . .
C31 C 0.2749(10) 0.2868(6) 0.8109(5) 0.0469(17) Uani 1 1 d . . . . .
H31 H 0.2478 0.2270 0.8409 0.056 Uiso 1 1 calc R U . . .
C32 C 0.4099(9) 0.3423(7) 0.8356(5) 0.0476(18) Uani 1 1 d . . . . .
H32 H 0.4759 0.3189 0.8820 0.057 Uiso 1 1 calc R U . . .
C33 C 0.4476(8) 0.4316(8) 0.7923(5) 0.0465(19) Uani 1 1 d . . . . .
H33 H 0.5384 0.4708 0.8100 0.056 Uiso 1 1 calc R U . . .
C34 C 0.2839(8) 0.6081(7) 0.6097(4) 0.0413(15) Uani 1 1 d . . . . .
H34A H 0.2059 0.6379 0.6315 0.050 Uiso 1 1 calc R U . . .
H34B H 0.2417 0.5451 0.5730 0.050 Uiso 1 1 calc R U . . .
C35 C 0.3353(9) 0.7087(7) 0.5671(5) 0.0507(18) Uani 1 1 d . . . . .
H35A H 0.3867 0.7677 0.6045 0.061 Uiso 1 1 calc R U . . .
H35B H 0.4063 0.6768 0.5410 0.061 Uiso 1 1 calc R U . . .
C36 C 0.2139(8) 0.7703(6) 0.5086(4) 0.0430(15) Uani 1 1 d . . . . .
H36A H 0.1561 0.7112 0.4734 0.052 Uiso 1 1 calc R U . . .
H36B H 0.1482 0.8105 0.5347 0.052 Uiso 1 1 calc R U . . .
C37 C 0.2757(9) 0.8590(7) 0.4643(5) 0.0475(16) Uani 1 1 d . . . . .
H37A H 0.3381 0.8177 0.4368 0.057 Uiso 1 1 calc R U . . .
H37B H 0.3379 0.9151 0.5002 0.057 Uiso 1 1 calc R U . . .
Cl2 Cl 0.1388(2) 0.9392(2) 0.39791(14) 0.0630(5) Uani 1 1 d . . . . .
C38 C 0.5234(10) 0.4997(7) 0.6422(5) 0.0493(19) Uani 1 1 d . . . . .
H38A H 0.5706 0.5609 0.6190 0.074 Uiso 1 1 calc R U . . .
H38B H 0.4803 0.4403 0.6038 0.074 Uiso 1 1 calc R U . . .
H38C H 0.5958 0.4622 0.6839 0.074 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.380(9) . ?
C1 C6 1.406(9) . ?
C1 N1 1.411(8) . ?
C2 C3 1.401(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(11) . ?
C4 Br1 1.909(6) . ?
C5 C6 1.391(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N1 C7 1.369(8) . ?
N1 H1N1 0.8800 . ?
C7 O1 1.207(8) . ?
C7 O2 1.350(7) . ?
O2 C8 1.457(7) . ?
C8 C9 1.518(8) . ?
C8 C15 1.532(8) . ?
C8 C19 1.538(9) . ?
C9 C14 1.384(9) . ?
C9 C10 1.396(9) . ?
C10 C11 1.392(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.402(11) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.523(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.521(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.524(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 Cl1 1.809(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.390(9) . ?
C20 C21 1.393(9) . ?
C20 N2 1.416(8) . ?
C21 C22 1.392(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.373(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.370(11) . ?
C23 Br2 1.915(6) . ?
C24 C25 1.399(10) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N2 C26 1.346(8) . ?
N2 H1N2 0.8800 . ?
C26 O3 1.212(8) . ?
C26 O4 1.360(7) . ?
O4 C27 1.463(8) . ?
C27 C34 1.518(12) . ?
C27 C38 1.533(9) . ?
C27 C28 1.541(10) . ?
C28 C33 1.390(12) . ?
C28 C29 1.395(10) . ?
C29 C30 1.393(11) . ?
C29 H29 0.9500 . ?
C30 C31 1.366(13) . ?
C30 H30 0.9500 . ?
C31 C32 1.395(12) . ?
C31 H31 0.9500 . ?
C32 C33 1.388(12) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.531(11) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.522(12) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.503(10) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 Cl2 1.780(8) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.9(6) . . ?
C2 C1 N1 124.2(6) . . ?
C6 C1 N1 115.9(5) . . ?
C1 C2 C3 120.3(6) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.0(6) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 121.8(6) . . ?
C3 C4 Br1 119.4(6) . . ?
C5 C4 Br1 118.7(5) . . ?
C4 C5 C6 118.9(6) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 120.0(6) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C7 N1 C1 125.7(5) . . ?
C7 N1 H1N1 117.2 . . ?
C1 N1 H1N1 117.2 . . ?
O1 C7 O2 125.7(6) . . ?
O1 C7 N1 126.0(6) . . ?
O2 C7 N1 108.3(5) . . ?
C7 O2 C8 117.8(4) . . ?
O2 C8 C9 111.6(5) . . ?
O2 C8 C15 103.0(5) . . ?
C9 C8 C15 109.7(5) . . ?
O2 C8 C19 109.4(5) . . ?
C9 C8 C19 114.2(5) . . ?
C15 C8 C19 108.3(6) . . ?
C14 C9 C10 119.1(6) . . ?
C14 C9 C8 118.8(6) . . ?
C10 C9 C8 122.0(5) . . ?
C11 C10 C9 121.1(6) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C10 119.0(7) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C13 C12 C11 120.8(7) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.0(7) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 120.1(7) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C8 116.6(6) . . ?
C16 C15 H15A 108.1 . . ?
C8 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
C8 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C17 C16 C15 110.6(6) . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 C18 111.7(5) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 Cl1 108.5(5) . . ?
C17 C18 H18A 110.0 . . ?
Cl1 C18 H18A 110.0 . . ?
C17 C18 H18B 110.0 . . ?
Cl1 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 119.8(6) . . ?
C25 C20 N2 116.4(5) . . ?
C21 C20 N2 123.8(6) . . ?
C22 C21 C20 119.7(6) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C21 119.3(6) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 122.3(6) . . ?
C24 C23 Br2 118.9(5) . . ?
C22 C23 Br2 118.8(5) . . ?
C23 C24 C25 118.6(6) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C20 C25 C24 120.2(6) . . ?
C20 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C26 N2 C20 127.3(5) . . ?
C26 N2 H1N2 116.4 . . ?
C20 N2 H1N2 116.4 . . ?
O3 C26 N2 127.1(6) . . ?
O3 C26 O4 124.9(6) . . ?
N2 C26 O4 107.9(5) . . ?
C26 O4 C27 119.6(5) . . ?
O4 C27 C34 109.6(6) . . ?
O4 C27 C38 102.3(5) . . ?
C34 C27 C38 111.5(7) . . ?
O4 C27 C28 108.9(6) . . ?
C34 C27 C28 115.4(6) . . ?
C38 C27 C28 108.4(6) . . ?
C33 C28 C29 119.1(7) . . ?
C33 C28 C27 119.4(6) . . ?
C29 C28 C27 121.3(7) . . ?
C30 C29 C28 119.9(8) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C31 C30 C29 120.9(7) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C32 119.7(7) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 119.9(8) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C28 120.5(8) . . ?
C32 C33 H33 119.7 . . ?
C28 C33 H33 119.7 . . ?
C27 C34 C35 113.7(6) . . ?
C27 C34 H34A 108.8 . . ?
C35 C34 H34A 108.8 . . ?
C27 C34 H34B 108.8 . . ?
C35 C34 H34B 108.8 . . ?
H34A C34 H34B 107.7 . . ?
C36 C35 C34 114.4(6) . . ?
C36 C35 H35A 108.7 . . ?
C34 C35 H35A 108.7 . . ?
C36 C35 H35B 108.7 . . ?
C34 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
C37 C36 C35 110.6(6) . . ?
C37 C36 H36A 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 108.1 . . ?
C36 C37 Cl2 112.8(6) . . ?
C36 C37 H37A 109.0 . . ?
Cl2 C37 H37A 109.0 . . ?
C36 C37 H37B 109.0 . . ?
Cl2 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?
C27 C38 H38A 109.5 . . ?
C27 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C27 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.5(10) . . . . ?
N1 C1 C2 C3 -178.9(5) . . . . ?
C1 C2 C3 C4 -1.7(9) . . . . ?
C2 C3 C4 C5 1.1(9) . . . . ?
C2 C3 C4 Br1 -177.7(5) . . . . ?
C3 C4 C5 C6 -0.4(10) . . . . ?
Br1 C4 C5 C6 178.4(5) . . . . ?
C4 C5 C6 C1 0.2(10) . . . . ?
C2 C1 C6 C5 -0.8(10) . . . . ?
N1 C1 C6 C5 179.6(6) . . . . ?
C2 C1 N1 C7 15.6(10) . . . . ?
C6 C1 N1 C7 -164.8(6) . . . . ?
C1 N1 C7 O1 -0.7(10) . . . . ?
C1 N1 C7 O2 177.6(5) . . . . ?
O1 C7 O2 C8 -2.1(8) . . . . ?
N1 C7 O2 C8 179.7(5) . . . . ?
C7 O2 C8 C9 64.2(6) . . . . ?
C7 O2 C8 C15 -178.2(5) . . . . ?
C7 O2 C8 C19 -63.2(7) . . . . ?
O2 C8 C9 C14 -164.5(5) . . . . ?
C15 C8 C9 C14 82.0(7) . . . . ?
C19 C8 C9 C14 -39.8(8) . . . . ?
O2 C8 C9 C10 19.8(7) . . . . ?
C15 C8 C9 C10 -93.7(7) . . . . ?
C19 C8 C9 C10 144.5(6) . . . . ?
C14 C9 C10 C11 1.4(9) . . . . ?
C8 C9 C10 C11 177.1(6) . . . . ?
C9 C10 C11 C12 -1.5(10) . . . . ?
C10 C11 C12 C13 0.3(11) . . . . ?
C11 C12 C13 C14 1.0(12) . . . . ?
C10 C9 C14 C13 -0.1(10) . . . . ?
C8 C9 C14 C13 -176.0(7) . . . . ?
C12 C13 C14 C9 -1.0(12) . . . . ?
O2 C8 C15 C16 -55.3(7) . . . . ?
C9 C8 C15 C16 63.7(7) . . . . ?
C19 C8 C15 C16 -171.0(6) . . . . ?
C8 C15 C16 C17 -166.1(6) . . . . ?
C15 C16 C17 C18 -173.3(6) . . . . ?
C16 C17 C18 Cl1 176.4(5) . . . . ?
C25 C20 C21 C22 -2.3(10) . . . . ?
N2 C20 C21 C22 177.4(6) . . . . ?
C20 C21 C22 C23 1.5(10) . . . . ?
C21 C22 C23 C24 -0.1(10) . . . . ?
C21 C22 C23 Br2 -179.3(5) . . . . ?
C22 C23 C24 C25 -0.5(11) . . . . ?
Br2 C23 C24 C25 178.7(5) . . . . ?
C21 C20 C25 C24 1.7(10) . . . . ?
N2 C20 C25 C24 -178.0(6) . . . . ?
C23 C24 C25 C20 -0.3(10) . . . . ?
C25 C20 N2 C26 173.3(6) . . . . ?
C21 C20 N2 C26 -6.4(11) . . . . ?
C20 N2 C26 O3 10.3(12) . . . . ?
C20 N2 C26 O4 -171.9(6) . . . . ?
O3 C26 O4 C27 5.8(10) . . . . ?
N2 C26 O4 C27 -172.0(6) . . . . ?
C26 O4 C27 C34 61.9(8) . . . . ?
C26 O4 C27 C38 -179.8(6) . . . . ?
C26 O4 C27 C28 -65.2(8) . . . . ?
O4 C27 C28 C33 -41.5(8) . . . . ?
C34 C27 C28 C33 -165.2(6) . . . . ?
C38 C27 C28 C33 69.0(8) . . . . ?
O4 C27 C28 C29 142.9(6) . . . . ?
C34 C27 C28 C29 19.2(9) . . . . ?
C38 C27 C28 C29 -106.6(8) . . . . ?
C33 C28 C29 C30 -0.1(11) . . . . ?
C27 C28 C29 C30 175.4(6) . . . . ?
C28 C29 C30 C31 -0.2(12) . . . . ?
C29 C30 C31 C32 -0.4(12) . . . . ?
C30 C31 C32 C33 1.5(11) . . . . ?
C31 C32 C33 C28 -1.8(11) . . . . ?
C29 C28 C33 C32 1.1(11) . . . . ?
C27 C28 C33 C32 -174.5(6) . . . . ?
O4 C27 C34 C35 49.9(7) . . . . ?
C38 C27 C34 C35 -62.6(8) . . . . ?
C28 C27 C34 C35 173.2(6) . . . . ?
C27 C34 C35 C36 -174.3(6) . . . . ?
C34 C35 C36 C37 -174.3(6) . . . . ?
C35 C36 C37 Cl2 -177.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N1 O3 0.88 2.06 2.892(6) 157.1 2_546
N2 H1N2 O1 0.88 2.02 2.863(6) 159.8 2_656

_refine_diff_density_max         0.929
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.076

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
